Picking sharp problems, increasing virality, and unique product frameworks | Oji Udezue (Typeform)

Oji Udezue is Chief Product Officer at Typeform and has held leadership roles at Twitter (Head of Product for Creation and Conversation), Calendly (CPO), and Atlassian (Head of Product for communication tools). He is well-known for bringing a product-led-growth (PLG) mindset to the companies he joins. Additionally, Oji mentors startups, is a Managing Partner at the Kernel Fund, and writes online about product management. In this episode, we discuss: • Oji’s “Where to Fish to Land a Unicorn” and “Zone of Benefit” frameworks • Why you need to find the “sharpest” problem • How to operationalize continuous customer discovery • Tips on optimizing onboarding flows • Freemium vs. gated offerings in PLG • Tactical strategies for making your product more viral • The concept of “forest time” and how it can provide clarity in your work — Brought to you by Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams: https://atlassian.com/lenny/?utm_source=lennypodcast&utm_medium=paid-audio&utm_campaign=fy24q1-jpd-imc Find the full transcript at: https://www.lennysnewsletter.com/p/picking-sharp-problems-increasing Where to find Oji Udezue: • Twitter/X: https://twitter.com/ojiudezue • LinkedIn: https://www.linkedin.com/in/ojiudezue/ • Substack: https://substack.com/@ojiudezue Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • Twitter/X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ In this episode, we cover: (00:00) Oji’s background (03:38) Oji’s “Where to Fish to Land a Unicorn” framework (05:26) Workflow quadrants (09:30) How product people can push frequency (12:28) Oji’s “Zone of Benefit” framework (14:49) How to find your ICPs (15:33) ICPs at Twitter (20:20) Oji’s philosophy on frameworks (22:31) Oji’s upcoming book (24:34) An explanation of “sharp problems” (28:31) Signs your problem is “sharp enough” (31:17) Discovery vs. continuous conversations (35:08) Customer listening (38:31) Onboarding fundamentals (43:49) Activated user milestones (45:47) The power of network effects (50:15) An explanation of virality and how to increase it (56:32) How to use “forest time” to zoom out and see problems in a new way (1:00:53) Lessons from Oji’s time at Bridgewater Associates (1:05:07) Why R&D teams need a larger system beyond Agile and design (1:06:57) Lightning round Referenced: • Where to fish to land a unicorn: https://ojiudezue.medium.com/where-to-fish-to-land-a-unicorn-in-b2b-saas-9bc93c96152c • Coda: https://coda.io/ • Atlassian: https://www.atlassian.com/ • Finding high-frequency customers (use cases): https://ojiudezue.medium.com/finding-high-frequency-customers-use-cases-53773a753bb5 • Evernote: https://evernote.com/ • Industry PM conference: https://www.industryconference.com/ • Typeform: https://www.typeform.com/ • Build better products with continuous product discovery | Teresa Torres: https://www.lennyspodcast.com/videos/build-better-products-with-continuous-product-discovery-teresa-torres/ • Pendo: https://www.pendo.io/ • Amplitude: https://amplitude.com/ • Dan Hockenmaier on Twitter: https://twitter.com/danhockenmaier • Seth Godin’s blog: https://seths.blog/ • A key ritual: Forest time: https://ojiudezue.substack.com/p/a-key-ritual-forest-time • Principles: https://www.principles.com/ • Dot Collector: https://principlesus.com/dot-collector-real-time-feedback/ • The Halo Effect:... and the Eight Other Business Delusions That Deceive Managers: https://www.amazon.com/Halo-Effect-Business-Delusions-Managers/dp/1476784035/ • Dune: https://www.amazon.com/Dune-Penguin-Galaxy-Frank-Herbert/dp/0143111582 • Foundation: https://www.amazon.com/Foundation-3-Book-Boxed-Set-Empire/dp/0593499573 • Foundation on AppleTV+: https://tv.apple.com/us/show/foundation/umc.cmc.5983fipzqbicvrve6jdfep4x3 • Unlox: https://unlox.it/ Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  Products who try to be viral just for what I call synthetic virality that fail. Because in the end, if you're synthetically viral and people get to the product and it sucks, that's it. You know Slack wasn't even viral, right? There was no synthetic virality. Slack couldn't even connect to organizations for the longest time. You could be working on the third floor and it's all using Slack on the fourth floor and you would have no clue. There's no way to share it with them. But what happens when you went to lunch, people are like, we got Slack and this is amazing. And people on the third floor are like, holy shit, when can we get it? Boom, boom, boom. This is the bedrock of virality. Build a great product that solves a sharp problem.

• 0:37Lenny Rachitsky?

  Welcome to Lenny's Podcast, where I interview world-class product leaders and growth experts to learn from their hard-won experiences building and growing today's most successful products. Today, my guest is Aji Udaisway. Aji has helped build and grow products at Microsoft. We worked on Windows Outlook, Hotmail and Internet Explorer. At Atlassian, where he was Head of Product for all their communication tools. At TalentLee, where he was Chief Product Officer. At Twitter, where he was Head of Product for Creation and Conversation. He's currently Chief Product Officer at Typeform, which I am a happy customer of. Aji has one of the broadest and most interesting careers in product, and he's also one of the most thoughtful humans I've met. In our conversation, Aji shares some of his favorite product frameworks and also why you should be really careful applying frameworks at your company.

• 1:20Lenny Rachitsky?

  We dig into what he's learned from TalentLee and Atlassian and Typeform on how to do product-led growth successfully, and also how to get really sharp with your ICP or ideal customer profile. Also, how to increase your product's virality and a concept called Forest Time, which I love. And even his favorite Nigerian food, which I am currently on the hunt for. With that, I bring you Aji Udaisway after a short word from our sponsors. You fell in love with building products for a reason, but sometimes the day-to-day reality is a little different than you imagined. Instead of dreaming up big ideas, talking to customers and crafting a strategy, you're drowning in spreadsheets and roadmap updates and you're spending your days basically putting out fires. A better way is possible.

• 2:03Lenny Rachitsky?

  Introducing Jira Product Discovery, the new prioritization and roadmapping tool built for product teams by Atlassian. With Jira Product Discovery, you can gather all your product ideas and insights in one place and prioritize confidently, finally replacing those endless spreadsheets. Create and share custom product roadmaps with any stakeholder in seconds. And it's all built on Jira, where your engineering team is already working, so true collaboration is finally possible. Great products are built by great teams, not just engineers. Sales, support, leadership, even Greg from finance. Anyone that you want can contribute ideas, feedback, and insights in Jira Product Discovery for free. No catch. And it's only $10 a month for you.

• 2:47Lenny Rachitsky?

  Say goodbye to your spreadsheets and the never-ending alignment efforts. The old way of doing product management is over. Rediscover what's possible with Jira Product Discovery. Try it for free at atlassian.com/leni. That's atlassian.com/leni.

• 3:07Lenny Rachitsky?

  Ajay, thank you so much for being here and welcome to the podcast.

• 3:11Speaker 00

  Thank you, Lenny. It's a pleasure to be here.

• 3:14Lenny Rachitsky?

  It's my pleasure. You've been a PM and a product leader at so many amazing and also just very different companies, with all with very different approaches to product and growth. And I think you have this really rare, broad perspective on what works in product and growth across a lot of different ways of doing it. And so I have a bunch of questions for you. I hope you came ready for that.

• 3:34Speaker 00

  I am ready.

• 3:35Lenny Rachitsky?

  Okay. I love it. Okay, so I want to start with frameworks. You've written and shared a bunch of really interesting frameworks for how to think about product and growth. And so I just want to dig into a couple of them. And one of them is around how to find big B2B SaaS ideas. And it's around finding the right workflow. Could you just share this framework and also just like how founders and also investors can use this idea to find big ideas?

• 4:01Speaker 00

  Thank you. So I think you're referring to where do you fish to find a unicorn?

• 4:05Lenny Rachitsky?

  That's it.

• 4:05Speaker 00

  And the thing behind that is that there's a, you know, people can find that on Substack and on Medium with my writings. But the premise is that there's a lot of risk in building startups, right? And the last decade of product management and startups has really focused on the method of building software in companies. We talk about the lean approach. We talk about fail fasts, YC, DuckTrain, and so on and so forth.

• 4:31Speaker 00

  And I think that that was a necessary phase for us because a lot of innovation was just the ideas of founders, unvalidated by customers, and we needed this inflection point in our discipline. People need to understand, though, that

• 4:47Speaker 00

  customer science is not the solution to everything. Otherwise, OpenAI will never have done anything, right? It's also innovation, all right? And so the problem space and the solutions to the problems to this place is still a big driver of success in building software companies. What problem are you really solving? And if you believe that the problem space is key, so what problems will predict success? Right? In B two B SaaS especially, which is much easier to circumscribe, is where I started to think about, look, how do you tell from the beginning? Because I'm an investor as well as an operator, right? Now, to segment this space, I think of two dimensions, you know? One is how many departments in the company

• 5:32Speaker 00

  does the workflow you're trying to solve apply to, right? Is it just a few or is it all of them, right? And the second is how intense or how frequent is the workflow executed? Is it daily? Is it weekly? Is it three times a week and so on and so forth? Now, if you draw a nice quadrant of these two things, then you can start to have some predictive power. Things that are useful in every department, I call everyone workflows, like things like collaboration, like Slack, email, calendaring, workflows, social knowledge in like Notion and so on and so forth. And then things that apply to single departments, I call niche and things that apply to, that's what I call niche, right? And then the intensity is about frequency. A month is not infrequent.

• 6:16Speaker 00

  Daily is super frequent. If you divide the market or the enterprise into frequency and into how broad the workflow is, you can actually have predictive power. And what I found by looking at The biggest companies, public and private, in each quadrant was that every one frequent workflows intuitively are the most profitable to work on, but also the hardest to get into because they're dominated by Microsoft and Google and very, very large companies. For example, one of my friends is the CEO of Coda. And so this is interesting because he's in that space for him to think about. And then the place where B2B SaaS really thrives is niche

• 7:03Speaker 00

  workflows that are highly frequent, right? High NAI is what I call it, you know, high frequency niche. And then there are the other two quadrants that are a bit more challenging and then you have to figure out how to navigate your way into one of the other two. If you are in one of the top two quadrants, high NAI and high everyone, and you solve a really important problem, workflow problem, you can probably turn into a billion dollar company. If you do the other two, there's some challenges that you have to go through and the framework sort of talks about how you should navigate those places into success. And I think it's very important because if this is true, and by the way, like I said, I did some validation on it.

• 7:45Speaker 00

  Founders can start to, before they invest years, start to think about what probability of success is. And if you're an investor like me or VC, you can start to think about how you deploy your money.

• 7:57Lenny Rachitsky?

  What are examples of companies in each of those quadrants? If you can frame this in your, I don't know if you have this in your head already.

• 8:03Speaker 00

  High frequency everyone workflows tend to be things that are done by the doorman to the CEO. So it's email, it's collaboration, it is writing, it is math, you know, all the basic things. And then last year, we spent a lot of time thinking about this. So Word, you know, we've had a, you know, word processing forever in the work, in the workspace. Things like Notion and Confluence are huge, a sort of evolution of that Slack email. Companies in that space, Google, Microsoft, Atlassian, et cetera. And the high NAI. Which is high frequency niche. You have things like Jira, right? You have things like, you know, tools for recruiters. You have Martech, right?

• 8:48Speaker 00

  You have SalesStack. And these are, we know the companies behind them, Atlassian, Salesforce, so on and so forth. And then in, in the, you know, low frequency everyone, you have things like maybe form tools. And actually, there are not that many of them, right? Low frequency everyone. Or even like expense, actually, the best is expensing, right? Not everyone does it all the time, but everyone essentially has to do some of it mostly. At least a lot of people. And then there's a low frequency niche, which is its particular department. So planning, which is done by FPNA, but done infrequently, things like that.

• 9:30Lenny Rachitsky?

  How frequent is frequent in your experience? Does it have to be like once a week at least? What is, do you think is that minimum bar?

• 9:38Speaker 00

  Frequent is every day, really. Or like multiple times a week. Infrequent starts to be like two times a week, once a month. And of course, there's a big interregnum in the middle of that.

• 9:51Lenny Rachitsky?

  It's interesting that there are examples of companies that succeeded in those lower quadrants of infrequent, say, the expensing use case. Do you have a sense of what it takes to win there? Cause I imagine most startups are in that area. And imagine founders are like, what can we do to win still?

• 10:05Speaker 00

  Well, this isn't the static framework in the sense that companies are not destined to be one of these things. The essence of strategy is to navigate from, you know, the, the, the curve of travel is essentially go from the lower to the higher, right? Atlassian is trying to go from high niche to high everyone with Confluence and with all the tools that they have. People below are trying to get into the high frequency niche by focusing on their core customer. So what it looks like, say, in, say, low frequency everyone workflow, something like that is, well, if some people are using it infrequently, but they must use it, well, that's a good thing, right?

• 10:45Speaker 00

  But then maybe you provide a, a module that is used by the finance department every day, right? And so suddenly you're moving into the high frequency everyone workflow. So it's about finding.

• 10:58Speaker 00

  A part of the organization that considers this mission critical and then solving their problems beyond the problems for everyone, for example, in that quarter.

• 11:08Lenny Rachitsky?

  Is there an example that comes to mind of either Calendly or Typeform or Lassine, where you pushed it further up the frequency direction or the everyone direction?

• 11:17Speaker 00

  For example, at Typeform, now this is real for me, Typeform technically is low-frequency niche or low-frequency everyone, depending on how easy it is to use and how it surrounds the customer. And one of the things that I'm trying to do as part of product strategy is to move it into high-frequency niche, high-end, which is a very productive place to be. So for marketers, for salespeople, I want to make sure that they think of us first, right? And because we are particularly good at customer-facing interactions, if they think that we are the way to win new business and to make money, then a portion of our audience, not every single one of them, will consider us high-end.

• 12:00Speaker 00

  And I think expanding that foothold is the way to navigate a business like that. You can see that with Poltrix, you can see that with SurveyMonkey, you know, lots of companies are thinking about how to further unbundle that market for a very, very specific kind of customer. And that is what they're trying to do. They're trying to hit the high-end, even for that sort of more generic workflow.

• 12:27Lenny Rachitsky?

  That's an awesome example. You also have this framework that I think you call the zone of benefit, which is around how much better does your solution have to be than the status quo? A lot of people are like, hey, look at this product, it's better than what you have now. And usually if you're like, ah, whatever, it's good enough. And you've had some insights on just how much better it needs to be for people to care. Can you share that?

• 12:45Speaker 00

  Honestly, the reason I like being a product manager is on any given day, I'm drawing from anthropology, sociology, behavioral economics, leadership, communication skills. I'm a trained, you know, I have a master's in engineering, so like I'm an engineer as well. I've done marketing and sales. So really pulling from so many things. And the reason I talk about the zone of benefit is ultimately what we're trying to do is impetus magicology to humans. That's it. Like if you really think about it, that's one essence of what we're trying to do. So the zone of benefit works as a framework because People will not pay for things that don't either really shrink the workflow that they're

• 13:30Speaker 00

  doing, or doesn't give them superpowers. So the same amount of time, but twice as much output. But the most important thing is that it has to be noticeable, right? If you do something 20% better, often people just around you, just as a human, people don't notice. And so for a product to make a difference, it has to be at least two, three more X for people to say, you know what, this is offering enough value for me to maybe make a switching cost and so on and so forth. And it really comes down to, look, economic theory tells us that people work for leisure. They work enough to afford their leisure. It's sort of broad, and I know some people don't necessarily do that, surely in the tech industry, people

• 14:15Speaker 00

  just love to work. But that is really it. You know, when you think about eight billion people on the planet, and this sort of benefit really hones in on the fact that if you're gonna help me work less, make about the same amount of money, then for you, for me to notice you, you have to accelerate me by three, three times for me to care.

• 14:35Lenny Rachitsky?

  Okay, awesome. So three times. So the idea there is you should feel like this is three times more productive in the thing that I'm trying to do, or it saves me three times. I don't know, like do it three times faster.

• 14:44Speaker 00

  Yeah, that's when people actually feel it. And they feel it enough where they part with money.

• 14:49Lenny Rachitsky?

  Awesome. And I think what's cool about this is it helps you identify the ICP for your product, if you're working a startup or even a new product within an existing product, to figure out who exactly is going to most benefit from this. Is that part of this?

• 15:01Speaker 00

  Yes, yes. Your best customers aren't price sensitive for what you're shooting for, because they get it, right? They fundamentally understand it. So yes, when you're shooting for ICPs, now every startup has, you know, like, marketing problems, getting an audience problem. But once you start getting a decent audience, over 100 people more, Uh. You should start to notice the people who are like, you know what this, I really care about this. And that starts to tell you a little bit about who who's your who's your target audience.

• 15:33Lenny Rachitsky?

  Would you be up for sharing the ICP of some of the companies you worked at, just to give people a sense of what would be a good ICP?

• 15:40Speaker 00

  I think for Atlassian, it's really kind of obvious. It's, you know, developers mostly. But it's tech teams writ large, because the fundamental of an R and D team is building stuff. And Jira helps the engineers who actually build stuff to track what they do and to give visibility to it so that it can be valuable to the organization. So that that is incontrovertible. So the ICP is really clear and had been clear for, you know, for Atlassian for a very long time. Calendly is this weird company where people don't see all the value. People think it's just casual scheduling. But really, the people who care about scheduling the most, and I don't mean calendaring, calendaring is very different from scheduling.

• 16:25Speaker 00

  People who care about scheduling the most are salespeople, because it's the lifeblood of them earning money. And marketers, because it's the lifeblood of them maybe learning about their customer. Recruiters, because it's the lifeblood of them attracting and scheduling the people that they need to do their job. So Calendly's ICPs were people who were scheduling with people who were not in the organization for some business reason. Typeform is marketers mostly, because

• 16:57Speaker 00

  Typeform exists to make the web talkative, to make it more human. And with Typeform, you can brand that conversation and actually make it conversational, because the one question at a time, the beautiful design. And so marketers feel like we help their websites talk to each other. Product people think we help their web apps talk to people they care about. Um. UX people feel the same way. So those are some. I I think the interesting thing is Twitter. I I.

• 17:27Lenny Rachitsky?

  I was gonna ask, I was gonna ask what the ICP for Twitter might be.

• 17:32Speaker 00

  So Twitter is actually more fun in terms of ICP because first of all, I'll talk about the thing that's not obvious about Twitter. Twitter has thirty percent of Twitter's customer base were unseen. There were media organizations. People like the NFL, the NBA, HBO, who wanted their content to reach more people to be in conversational spaces. And they were essentially business customers and not seen in the in the conversation pool. It's not obvious, but we interacted with them all the time. And we rev shared ads for their their videos, right?

• 18:11Speaker 00

  Because we're making content all the time. And so Twitter was a way to extend the monetization of that content that inventory that already had. But when you go to the consumer side of Twitter, who are what was the ICP? Well, actually Twitter understood, and this is sort of reflected in what Elon Musk is doing these days, that he doesn't seem to understand. And if you ask anyone who was at Twitter, you will you will see the understanding in their eyes and the fact that he doesn't understand because Twitter's ICP is bifurcated. On one side, it is the most accomplished people in the world, right?

• 18:49Speaker 00

  The people who have something to say. This is why there's Neuro Twitter, there's Weather Twitter, there is Cancer Twitter and so on and so forth. In fact, if something breaks, some new innovation happens in the world, it probably breaks on Twitter before it breaks anywhere else. Because these are people in informal communities following each other and sharing their results. So basically, there's this big circle of experts. We break down into celebrities, we break down into luminaries, leaders and so on and so forth. That's the ICP. Now, how does Twitter work? These people attract the other ninety percent who listen to these people.

• 19:29Speaker 00

  But also, they need to create their own informal communities around the things they're passionate about. And have this memetic relationship with the luminaries and the experts. And that is sort of the planet Twitter. Experts on one side, humans who need to connect with the things they're passionate about. The people who are like them. That is the ICP of Twitter. The people who have something to say in those two categories.

• 19:58Lenny Rachitsky?

  Are you happy you're not working on Twitter anymore?

• 20:00Speaker 00

  I am ecstatic.

• 20:03Speaker 00

  I'm ecstatic. It seems like such a shit show. You know, no shade on anything or anyone like purposely, but you know, look, what's happening is evident. So I don't think I have much to say about that.

• 20:18Lenny Rachitsky?

  Yeah, what a wild ride over there. Zooming out on the frameworks question. When I asked you ahead of our chat about what frameworks you love and anything you think would be interesting to share. You had a really interesting response, and so I'd love for you to just share your perspective on frameworks broadly.

• 20:34Speaker 00

  Yeah, look, I'm two things simultaneously. One is I actually, I like frameworks. The way that I try to express them is mental models, right? Because the essence of a framework or a mental model is that it is a shortcut. It packages some dense thinking into a way for you to approach a problem or to approach an opinion and so on and so forth. So I do collect them. But I think that what's important, a fairly important management, is to have the ability to understand the fundamentals or the empirical relationship that constructs a framework in the first place. In math, you would call it like being able to derive the equation.

• 21:16Speaker 00

  And the reason that's important is because there's so much uncertainty in what we do. Like product management isn't a science. In fact, programming isn't even a science, really, because if it was, we'd treat it differently. So the art of building, say, a software company that is profitable is.

• 21:34Speaker 00

  Not scientific. There's a lot of uncertainty, a lot of unknowns, there's timing issues. So I guess while I love mental models, while I love frameworks, what I want people who listen to me, and maybe listen to you to understand is you have to go deeper because as situations change, like I, you know, as an investor and advisor to startups, I advise differently if you are just starting, if you're in the middle, and if you're scaling, right? In the book that I'm writing on product, I actually make that distinction a lot in the book, which is which stage are you? Because then the thing that applies to you is different. If you understand the fundamentals, you'll be able to use frameworks in a much more productive way

• 22:18Speaker 00

  because you'll adapt it to your stage, you'll adapt it to the problem. And I think that's really important. I see lots of people using frameworks very blindly. And I think that's harmful to them and harmful to their businesses.

• 22:31Lenny Rachitsky?

  What a great segue to where I wanted to take us next, which is around the book that you're writing, which is my understanding is it's product management for product-led growth. And I'm on your waitlist to find out when it's out. And I saw that the other day, you asked people for their advice on what to call the book. Do you have any favorites at this point of what you might title it?

• 22:50Speaker 00

  Well, first of all, like there are two things happening with the book. One is I believe PLG is, I have maybe a different definition of PLG, but I think the way that we are basically adapting products to the, the, the consumer or to the business professional and using the product itself to sell the value proposition is really key to transitioning from what we used to do 20 years ago to today. Basically, I think even enterprise companies will tend towards a consumer-type product management over the next decade than the other way around. That's my bet. And so let's call that PLG just writ large. And also I think product management is set for growth.

• 23:33Speaker 00

  So obviously that's good for you, Lenny, because everyone needs to know how to do this. It's the integrative art within building software and software is leading the world. The book, I want to get very practical, what matters about doing those two things well. And the best titles coming up are

• 23:54Speaker 00

  My original title was Building Rocket Ships. So it's like, how do you think through all the different things you need to build a really successful software company? Think about the practice, think about the business, meld those two things together. So a lot of people love that title. Well, there's a huge variation in submissions. So I think we're going to do that one more time and offer more options before we nail down the title of the book. So till TBD.

• 24:22Lenny Rachitsky?

  Cool. All right. I'm excited to see where you land. So let's just spend some time on PLG. I feel like this is your bread and butter as a product leader. You've worked at some of the most successful PLG companies and I think you have some of the most unique perspectives on what works and doesn't work. And I saw you shared a preview of what you're going to be sharing the book. And so there's a few things there that I thought were really interesting that I haven't seen other places when it comes to PLG. So I was just going to dig into.

• 24:45Speaker 00

  Very.

• 24:47Lenny Rachitsky?

  Absolutely. The first is this framing that you had for where to start and how to focus with your PLG problem. And you described it as starting with a sharp problem. Can you talk about what that means?

• 24:59Speaker 00

  Yeah.

• 25:02Speaker 00

  So I'm trying to connect dots. The sharp problem is a little bit of that whole quadrant framework, which is what problem are you going to work on? I think that problems have predictive power of success if you actually solve the problem. And this is different from I have an idea. Yeah? I think that a lot of innovation can come from inspiration, or the best inspiration comes from understanding customers and their problems. So my advice to founders is pick a problem that is materially felt by your customers. Pain points that steal their time, their energy, their money, their focus, their inability

• 25:47Speaker 00

  to afford their leisure. If you can solve those kinds of problems, and look, I know that it's broad, but because it requires insight. You know, the best founders often are people who felt a problem. Understand it, understand that it's really difficult. I understand that there may be like five, 10, 20 billion people who feel it and they don't want to solve that problem. Versus, I feel a problem, but only a hundred thousand people care, in which case maybe uh it's not that intense anyway, uh unless you can charge them thousands and thousands of dollars. So pick those kinds of problems. If you, if you, if you have the narrative in your head that

• 26:29Speaker 00

  if you really solve this, people will pony up. That's what I ask people to find. Too many of us just have a sharp idea. Look, I've built a startup on a non-sharp problem. And I, I, I knew how it felt. Well, I also know working in companies that are solving sharp problems, how it feels. It's a, it's a huge tailwind to do that. In fact, when you work on sharp problems, it's hard to fail because you can make mistakes and the, the customer's obsession will carry you. But if you work on something that doesn't have a sharp problem, mistakes can kill you because essentially you're having to pay a lot for marketing, you're having to pay a lot for word of mouth. People, when they get poor, they don't care about it, like recessions.

• 27:15Lenny Rachitsky?

  Coming back to something you mentioned earlier, but just like how much pain it needs to be for people to care? Or how much pain it needs to solve versus the status quo, I think is a really important element of this. I think most founders like, no, I need to solve a problem, but usually it's not painful enough or it's not solving it enough. Give an, either an example of something that you've tried or you've seen of just like, that was a sharpish problem, but not sharp enough? And people didn't care. Some, either a company worked or a startup you advised of just like, okay, that wasn't, it wasn't sharp enough.

• 27:46Speaker 00

  I don't want to create enemies because I know a lot of founders, but, but I, here's one, here's one. I don't know if you remember during the pandemic, um

• 27:56Speaker 00

  this venture studio, um by, I think one of the ex-founders of Evernote created Mm-hmm Camera.

• 28:04Lenny Rachitsky?

  Oh yeah, absolutely. Yeah.

• 28:05Speaker 00

  Yeah.

• 28:06Lenny Rachitsky?

  That a great video.

• 28:07Speaker 00

  It was fun, but I don't think it was a sharp problem.

• 28:11Speaker 00

  Right, like you, it was fun, but yeah, it didn't, it didn't change the world of your Zoom camera. Didn't change the world of your collaboration.

• 28:25Speaker 00

  And so I think that's one example of a non-sharp problem, for example, for most people.

• 28:31Lenny Rachitsky?

  What are signs that it's sharp enough, just like in your experience? I know you talked about it steals your time, energy, money focus. What are flags that like this is sharp enough in your, in your experience?

• 28:42Speaker 00

  I think there are two ways to think about it. If you're, if you're on the trenches as a founder, the easiest way to, to, to map out a sharp problem is draw the current approximate average workflow for your target customer, at least what you think is a target. And then draw the workflow after they've used your software and see how shorter it is, how much shorter it is, yes or no? And I try to measure those lines, if you draw them as horizontal lines, try to measure those lines and see if it's much shorter. If it's two X shorter, three X shorter, that's, so let's say pre-customer, that is the best way to hone in on it.

• 29:24Speaker 00

  Post-customer, you should talk to the people who are most enthusiastic and derive their workflow and their workflow change. And try to measure that. I think that's how you figure out if it's a sharp problem or not. The other thing that we talk about in startup, you know, or super early stage world is I call it the whites of their eyes. Right, when you take a problem and you share it with someone who is, it's, is, is going to affect their workflow. And I use the word workflow a ton because I don't use specs anymore or use cases. I think workflows are the unit of productivity. When you see people's eyes get big.

• 30:02Speaker 00

  And expose more whites to you.

• 30:05Speaker 00

  You you're probably on to something. It's not enough. That's not a workflow thing. That's an excitement thing. Um, but people often react that way when you're solving a really sharp problem for them. And then people spontaneous will bring up money that this like, when can I pay? When can I? Those kinds of things give you an indication.

• 30:23Lenny Rachitsky?

  Two other versions of the uh showing more whites of your eyes, which I love. Another two other versions of that I've heard is one is you you see their pupils dilate. And they're just like, whoa, I need this now. And then the other is someone described it as you see this nod. Of as you're talking, they're just like, oh, I get it. I get this. And then they're like, okay, we need this in our in our in our company.

• 30:46Speaker 00

  I'm a little over those ones because sometimes it's just excitement and this noise. And so the things I said previously about workflow um compression. Or capability uh inflation. I think those are more reliable, which is all all about like customer research and customer conversations. And that's what I would focus on. Yeah, but I I'm saying all this from mistakes I've made. Right? Basically, so I feel like this is scar tissue, which is what I'm trying to pour into the book.

• 31:17Lenny Rachitsky?

  Speaking of talking to customers, another one of your big bullet points in the book. Is around continuous customer discovery. And I'm curious what you found to be successful in actually doing that. You know, a lot of people talk about it when you keep talking to customers, get feedback constantly. What actually works in your experience?

• 31:34Speaker 00

  Yeah, I feel like um. All of work management is about discovery these days. Everyone talks about it and. I want to make a distinction. I think discovery is when you. Use com- customer conversations to understand a very specific thing. That you want to optimize for their workflow that you want to optimize further. And then you call the people who are most likely to be affected and you do use. Various research strategies uh to talk to them. There's a version of that also that is what I call continuous conversations, which is. Accountly and a type form. Which will do more and more of.

• 32:16Speaker 00

  You should organize it so that your PMs, your designers, your engineering managers and your PMMs are constantly talking to customers by default. Meaning that customer conversations show up on their calendar every week, automatically, without them getting involved. And then they're trained on how to have the conversation. Because the death of customer discovery is friction. If you ask individuals to do customer discovery, they will not do customer discovery. This is a thing that dies in an innovative company. Because it's very difficult to actually talk to the right customer, not talk to any customer, talk less of the right customer continuously.

• 33:01Speaker 00

  But there's a third thing that I like to talk about, which is customer listening. In fact, I'm going to talk about is that industry in October, the PM conference. Customer listening is different. It's not really discovery. It is the scarfing up of customer signals that are happening constantly anyway. So people are talking on social. People are talking on app stores and G2 crowd. People are, if you have a churn, instrumented churn survey, people are talking. If you have MPS, people are normally giving you the scores where they're putting in the verbatims. If you have a bug report, which we had at Atlassian, people are filing bugs.

• 33:46Speaker 00

  You know, developers love to file bugs, so of course we have that for that audience. And then if you go to Zendesk and customer support, people are either talking about one thing all the time or a range of things. And you can see the frequency distribution. And of course, in Salesforce, you have closed one. These are all things happening no matter what you do. Whether you're listening or not, you're getting these signals. One of the big hairy audacious goals of product management is being able to process these signals efficiently. We did it in a certain way at Calendly, which I jury raked together through, you know, workflows and Slack. And then having individuals triage those things.

• 34:28Speaker 00

  And if you can do that hard, and you know, at industry, I'll talk a little bit about how to do it. It's not exactly discovery. It is what matters. Right? Our job is to meld customer delight with business ambition. And it feels essential beyond discovery that you are listening and you're understanding what matters from a customer delight perspective. And I don't think many of us do this really well. I've tried to do it everywhere I've gone, Twitter, uh, of last year and Calendly, now at Typeform, but it still feels like something that the industry can get better at.

• 35:07Lenny Rachitsky?

  This touches on advice that Teresa Torres teaches around continuous customer discovery. And she actually had a really good tactic that I'll share here that stuck with me about how to actually do this. So the way she recommends companies do this is have a little pop up on your site, asking visitors, like, we'd love to talk to you and get your feedback on our product. And it just links them to a Calendly to book a meeting and that's how it shows up on the calendar.

• 35:30Speaker 00

  Yeah, that's what we did at Calendly, you know? But I will say, so a couple of caveats. We did that in the community. We had, you know, community to Calendly to come. And we understood that that was a self-selected group, but it was still important to talk to them because they were still representative. And of course, you, you should do it in the product. The challenge of that approach is always, is it the right customer? Right? And you know, the pro con of that is talking to one customer is useless. Talking to a hundred is super useful. And so the challenge is, are you targeting the right person? So some intelligence upfront and like who to show it to and why you're showing it to them?

• 36:13Speaker 00

  So that they can come is interesting. Very particularly effective, by the way, for growth. Because if people don't activate or churn, they don't want to talk to you. But if you can present that thing out in their activation or conversion journey, they might actually talk to you. And so that's really key. So I a hundred percent agree with Teresa. That's exactly what you should do for not even, I wouldn't even call it discoveries for listening. All right. And some of it can be discovery. Um, yeah, I, I think that's exactly what you should do.

• 36:45Lenny Rachitsky?

  As you're talking, I'm realizing I'm using most of the products you've helped build. I'm on Twitter a lot. I use Calendly a lot. I use Typeform as my default survey tool.

• 36:55Speaker 00

  I saw that. My team is really excited to use it.

• 36:58Lenny Rachitsky?

  You're, you've impacted my life in so many ways, Ajay.

• 37:02Speaker 00

  I think you owe me money, Lenny.

• 37:03Lenny Rachitsky?

  What do you need? How much? How much? Give me your Venmo QR code. It's online.

• 37:11Lenny Rachitsky?

  You fell in love with building products for a reason, but sometimes the day to day reality is a little different than you imagine. Instead of dreaming up big ideas, talking to customers and crafting a strategy, you're drowning in spreadsheets and roadmap updates and you're spending your days basically putting out fires. A better way is possible. Introducing Jira Product Discovery, the new prioritization and roadmapping tool built for product teams by Atlassian. With Jira Product Discovery, you can gather all your product ideas and insights in one place and prioritize confidently, finally replacing those endless spreadsheets. Create and share custom product roadmaps with any stakeholder in seconds. And it's all built on Jira, where your engineering team is already working.

• 37:55Lenny Rachitsky?

  So true collaboration is finally possible. Great products are built by great teams, not just engineers, sales, support, leadership, even Greg from finance. Anyone that you want can contribute ideas, feedback and insights in Jira Product Discovery for free. No catch. And it's only $10 a month for you. Say goodbye to your spreadsheets and the never ending alignment efforts. The old way of doing product management is over. Rediscover what's possible with Jira Product Discovery. Try it for free at atlassian.com/leni. That's atlassian.com/leni.

• 38:31Lenny Rachitsky?

  Going back on track, another important part of the book that you're writing is is around onboarding and something that I talk a lot about on this podcast is just the power of onboarding and how impactful it is to retention and so much of the eventual success of your product and how customers use it. And so I'd love to hear just your advice on what you think is really important. Like, I guess, why onboarding is so important in success and PPG and also just like, what tactics have you found to be really effective?

• 38:59Speaker 00

  Let me talk about a few fundamentals. Onboarding is a substitute for sales and,

• 39:08Speaker 00

  you know, all these account management teams for millions of customers. The task is how do you make it approximate a human and how friendly a human is and how approachable a human is? Because if you can do that, then you can process thousands and thousands of customers very quickly. Onboarding is an exercise in understanding the mindset of a buyer, of an evaluator. It's nothing more than that, meaning that the province of understanding is social psychology. It's not really product. It's buyer psychology. I guess, who knows a lot about this stuff? It's people in the offline industry, the people who stock shelves,

• 39:49Speaker 00

  the people who provide inventory online and so on and so forth. They are extraordinarily good at this. So the reason I say this is to divert people who are gross to really find where to source their inspiration from for onboarding, first of all. If you think about this as intentful in that way, which is people come not knowing anything about you, and then they progressively develop confidence that you are the tool of choice, you don't have to break it down into how does that journey go through a mind, the average mind, anyway? And how do you assist each part? One is value proposition, understanding. One is trying

• 40:30Speaker 00

  to see if it's simple enough and provides enough value. One is kicking tires, and one is making the choice that this is something I'm going to go forward with. How does your onboarding support all of these things? Now, I think there are two parts of onboarding. One is Mandatory, the setup. It has to be spare. I try not to make it more than three screens, but it's about. How do you say what this does? And provide the essential setup that your customer needs to be successful. At Cali, for example. We asked them about connecting their calendar. And setting some defaults, is it nine to five or whatever that is?

• 41:16Speaker 00

  Those two things set up all the future success. And if we made it optional, more people would fail. So it's information and. The essential setup. And it should be as short as possible. Then there's a whole other set of things that should be optional because they're not necessary for everyone to be successful. Well, they're beneficial if people are curious. And also it can be. What we call a random access, so people can get back to it anytime they they want, like you're there feeling help. And so if you divide onboarding into those two things and then figure out what to put in one and what to put in the other. I think you can be quite successful. And this is just the tip of the iceberg that I get into in the book.

• 41:56Lenny Rachitsky?

  Are there any examples of really big onboarding wins, things that really helped with conversion or activation that come to mind?

• 42:01Speaker 00

  Well, I think keep it short is one big win. Um, the fewer things, the better that are essential that everyone has to go through. It's unclear if all those click throughs go here, go here, and all those things work.

• 42:16Lenny Rachitsky?

  Hmm, the wizards, yeah.

• 42:17Speaker 00

  Yeah, the wizards have had, in my experience, limited. Benefit. Um. So much as just directing people to the one thing that they need to do post mandatory onboarding. Having examples, not ten, one or two of what good looks like. Is particularly powerful because it's mimetic. People see, oh, okay, this is exactly what I'm shooting for. Uh, is very powerful. In terms of trial and conversion. Letting people understand and being very clear about where they are in the trial cycle, whether you want them to pay for it now or they need to pay for it later after seven days, having them understand that really clearly so they know where they are versus

• 43:02Speaker 00

  they feel like they're completely at sea, I think is very important for conversion. I think there are a few things like that, but I also want to mention that it's different for every product, right? Depending on where you are in the quadrant and the amount of augmentation and problem solving and how sharp the problem is, you might want to adjust your approach. And this is the kind of thing that there is no, there's some fundamentals, but it's not necessarily this one size fits all. In fact, at Typeform, we're trying to maybe invent new, a new twist on freemium just because of some of the things we're seeing for our particular customers. And so, you know, these are, for me, some new

• 43:46Speaker 00

  learning as well as I go through each different product.

• 43:49Lenny Rachitsky?

  Along these lines of onboarding activation and getting a user activated is really important. And I'm curious, do you have an example of what an activation milestone was at Calendly or Twitter or Typeform, just to give people a sense of like, here's a good example of an activated user milestone?

• 44:03Speaker 00

  I think this goes back to, you know, people, the pendos and the amplitudes of this world. You have to sort of think through your aha journey, right? Like at Calendly and also at Typeform, we have three thresholds of increasing activation, right? And we just try to make sure that people go through each one, as many people as possible. And frankly, we try to figure to drop off between the increasing definitions of activation. So at Calendly, we want to make sure you've created your first meeting, right? But then if you've created five within a week, that's really much more powerful. At Typeform, it's really about have you published a form and have you gotten responses? And have you gone

• 44:47Speaker 00

  to look at what the responses mean in the insights page, for example? At Twitter, it is, are you following anyone or are you being followed, right? Because that verb, follow, is the way you start to construct. Your informal community. Remember what I said is Twitter is for people who want informal community around a topic. And that is not, you know, Facebook is about who do you know? Twitter is about who do you want to know who's passionate about what you're passionate about? And so if you haven't set up your follow graph at all, you're not going to really activate. It's not going to be compelling for you.

• 45:23Lenny Rachitsky?

  Awesome. Those are great examples. It's funny hearing the Twitter activation milestone out of context. Sounds so creepy. Have you followed anyone? Or is anyone following you?

• 45:31Speaker 00

  Yeah, because a lot of people go in and then they don't, they tweet into the void, or they don't feel like they have a voice.

• 45:36Lenny Rachitsky?

  Right.

• 45:37Speaker 00

  But that's not the most important thing. Most important thing is are you getting content that you're interested in? That makes you want to come back and see more and follow is a huge part of doing that.

• 45:47Lenny Rachitsky?

  Yeah. Just on the point of Twitter, I don't know if this goes anywhere, but it's crazy how it keeps going, no matter how much destruction is happening all around.

• 45:57Speaker 00

  Uh, you want me to talk about that? Because I want to talk about.

• 46:00Lenny Rachitsky?

  Please.

• 46:01Speaker 00

  So, uh, you know, one of the things that they, they, they, I want to say they, one of the things I learned early on is network effects.

• 46:11Lenny Rachitsky?

  Yeah.

• 46:12Speaker 00

  Network effects, let me define it. Network effects is when you create value for passive members by other people joining the network. So I am by myself. I have done nothing. I'm at home chilling. Well, one person joins the network and immediately I gain benefit. Okay. So think about Facebook. If there are eight billion people on Facebook, it means that all of a sudden I can reach everyone on the planet. And so the more people on Facebook, the more it's valuable to me regardless of my effort. That's network effect. If I'm

• 46:52Speaker 00

  into Word, Word, you know, Word processor, you know, Microsoft Word. And the more people who use that file format, it means that the more Word documents I can read. And so I did nothing. So by increasing the people who adoption of Word, I gain benefit, network effect. That's what it is. So Twitter, you know, and then this is the mental model of critical mass. Network effect is about critical mass. You hit a critical mass and sometimes that's not mathematically defined. And then you've hit network effect because people want to come because people are already there. Right? So Twitter has hit critical mass and lots of your favorite social networks.

• 47:37Speaker 00

  Network effects is a feature by itself and it's the most powerful feature. A good way to illustrate the power of network effects is Twitter did not die because threads came up, came about. Right? That's the power of network effect. In fact, the last telegram was sent in 2016. Over a hundred years after it was invented because of network effects. It had to be manually closed down. I believe Friendster is still alive. So we have to be really clear that it's really hard to kill a network effects business now. How do you, how do you actually accomplish it if you were to accomplish it? Well, the revenue side of any social network is vulnerable to attack.

• 48:22Speaker 00

  So for example, if advertisers stop being on Twitter, for example, they're not gone because again, network effects affects them. They want to go where their eyeballs are. But if for some reason they disappeared, then while the people will continue to come, the ability to have money to improve the network will disappear. And that is sort of a negative spiral. What is very, very hard to kill business is hard to kill software that has reached network effect. Although you can kill businesses that have reached network effect.

• 48:56Lenny Rachitsky?

  That's a really important and interesting insight. I think what's even especially interesting about Twitter is Elon and the team have kind of like removed every other benefit of Twitter, like the brand gone. Employees, eighty percent gone, like every part of it is being cut off except for the network effects. And so it's a really cool case study. Dan Hockenmaier tweeted this, was a previous guest of just like, it's a good case study of what is just the power of just network effect.

• 49:19Speaker 00

  That's right. I think that people will, you know, when I did a really interesting course at Berkeley Business School, about technology companies and so on. And this is a perfect case study on network effect, the best I've ever seen. It is incredible.

• 49:35Lenny Rachitsky?

  Yeah, it's well, Threads isn't able to get there quickly, unlike what it felt like initially.

• 49:42Speaker 00

  I mean, Threads will prosper, I believe. And again, you know, it'll just be another click for advertisers who understand the Facebook marketplace versus Twitter ad marketplace is much harder to access. And so I think the way Threads wins is the is a revenue spiral versus the like pure activity spiral.

• 50:02Lenny Rachitsky?

  Interesting. Where essentially they find ways to, even with lower base, make generate revenue, which drives advertisers, drives more investment.

• 50:10Speaker 00

  Correct, correct.

• 50:11Lenny Rachitsky?

  Awesome. All right. That'll be funny, fun story to watch. Kind of along those same lines. I want to chat about virality a little bit. You worked on some of those viral products out there in B to C, as Twitter is an example, but also in B to B, which is really rare and interesting. And I know there's no silver bullet for increasing virality, but everyone's always wondering, how do I increase the virality of my product? So I'm curious, anything you could share, any tactics that you've seen work to increase the virality, especially of a B to B product?

• 50:35Speaker 00

  Well, as is my style, I want people to understand what virality is in the first place, because I think people have misconceptions about it. People think virality is some, you know, Hotmail's tag at the bottom that says, go get a free account. Virality is really when the word of mouth of a product is high quality. That's really the essence of it. Let me rephrase that. It's when customers market your product, right? And

• 51:06Speaker 00

  That is incredibly powerful, but also that's incredibly actionable, if that makes sense. There are products who try to be viral just for what I call synthetic virality that fail. Because in the end, if you're synthetically viral and people get to the product and it sucks, that's it. That's the end. Even Hotmail, for example, people talk about the viral tag. I don't know. You know what I'm talking about?

• 51:32Lenny Rachitsky?

  Absolutely. The bottom, like, yeah.

• 51:34Speaker 00

  Yeah, the bottom. But remember, it wasn't just that. It was one of the first webmail things. And webmail was revolutionary because you didn't have to have a POP3 client and lose your email across multiple devices. It solved a lot of really good problems for customers at the time for email. And so when they arrived from the free account, it was like, holy crap, this is amazing, right? And so let's do that. Uber doesn't have any weird viral traps, but it compresses the workflow of Helene Cab so much that it's viral, if that makes sense. In fact, there was this time where Austin kicked them out for,

• 52:17Speaker 00

  and other apps came in and filled the void, and then it came back after the year and just crushed everybody. There was not no campaign, it was just viral by itself. So that's what virality is. So then the question is, how do you increase it? Well, look,

• 52:32Speaker 00

  fundamentally, build a great product that solves a sharp problem and build it really well. If you do this, this is the bedrock of virality. If you don't do this, there's no viral tactic that will work in a sustained way, right? It will fizzle. But if you do this, you can layer on synthetic virality, strategies for referrals, strategies for coming back into the app and creating an account, right? Remember, before Cali, there was Acuity Scheduling, there was other things.

• 53:09Speaker 00

  The difference was Cali was so well-made, so simple for schedulers, so respectful of schedulers' time, not just the creators' time, that the virality worked. It did not work for others who sucked.

• 53:26Speaker 00

  X.ai and other places, they weren't that good. You have to be good to be viral.

• 53:33Lenny Rachitsky?

  That is such an important insight that everyone looks at Calendly like, of course, you're sharing calendars with everyone, it's gonna go viral. That's like, what a cool trick. But your point is so interesting that there's previous versions of that, but the product itself wasn't great, the experience wasn't great, it was too complicated, it didn't work. And that's what made it so viral.

• 53:51Speaker 00

  Yeah, there may be several things I think affect virality. But I think that this is the nugget that people need to take away. That is the foundation, the bedrock of all of them, right? Like, customer support actually affects virality. Like, if you have fanatical customer support, people will love it. Viral tactics, like, you know, the page that says, oh, get an account and so on, doc, you know,

• 54:15Speaker 00

  you know, all these signing doc, you know, Calendly and so on and so forth. You know, network effects, as, you know, in Calendly, you have these green dots. If you and a person have Calendly, it tells you when you're free. All network effects, really high-quality execution, synthetic virality, all contribute to net virality. But the fundamental is exactly what we just discussed.

• 54:38Lenny Rachitsky?

  Just gotta get it all right. No big deal. I, um...

• 54:42Speaker 00

  Build the best product possible. Honestly, if you want to be viral, that's, you know, Slack wasn't even viral, right? There was no synthetic virality. Slack couldn't even connect to organizations for the longest time. Why? You could be working on the third floor and so on, using Slack on the fourth floor, and you would have no clue. There's no way to share it with them. But what happens when you went to lunch, people are like, we got Slack and this is amazing. And people on the third floor are like, holy shit, when can we get it? Boom, boom, boom. Great product first is virality.

• 55:14Lenny Rachitsky?

  Seth Godin has this phrase I always come back to. If you want to make your product remarkable, something people want to remark about. And that's basically the core word of mouth.

• 55:22Speaker 00

  Yes, yes, yes.

• 55:24Lenny Rachitsky?

  I was watching a talk you did on this kind of topic. And you have this great phrase that you sort of touched on, but I think it's so good. And I just want to make sure we highlight it, which is that virality is customer augmented marketing.

• 55:35Speaker 00

  Mm-hmm. Yeah, I think is the thing that I started with first. It's, it's when your marketing is essentially done by your customers, right? Because what it does, it affords you the ability to spend less on marketing.

• 55:49Speaker 00

  And you can either up-level your marketing execution with that, or save money that you can put in the product. Atlassian spends...

• 55:58Speaker 00

  Maybe like ten, twenty percentage points less on marketing than the equivalent competitors because it's viral. And also because of its network effects at this point as well, say Jira. And so it's customer oriented marketing. Your customers are either forcing other people to adopt it or shaming them into adopting it or fomenting them into adopting it. So yes, virality is essentially customer oriented marketing, which gives you options.

• 56:28Lenny Rachitsky?

  I love that phrase. I'm gonna use it now. I have just a few more questions before we get to our very exciting lightning round. And these are kind of random two topics that I wanted to chat on. One is this concept that you call forest time. It's a post you wrote about the importance of forest time. Can you just describe what that is and why it's so important? And then also just how to do this?

• 56:49Speaker 00

  I operate, I'm an operator right now, meaning that I'm building things. I work for a company, but I also advise and invest, which is different. When I'm advising, I'm looking from above, from outside. I have a bird's eye view and I'm able to say, you know what? This will work, this won't work. What have you done? Can I look at the results and then, you know, cycle the advice based on what you're seeing and what I'm seeing? When I'm operating, I'm building a team, I'm hiring, I'm managing. All the thing, Eileen, I shout out that hates sometimes. And that's what I'm doing. When you are operating, you have the fog of war.

• 57:32Speaker 00

  Like it is so intense that you don't have the attention to have a bird's eye view constantly. And so forest time is the idea that you make time within your week, within your month to see the forest for the trees. Most of the time when you're operating, you're seeing the tree, which is a problem for you. But sometimes you need to see the forests so you can figure out if there's an alternate path different from the one that you are currently on your campaign. And so it's time to elevate, to get some bird's eye view to see the entire landscape and see your alternative paths through the current problems that you're escaping. And I think that it has to be very intentional.

• 58:15Speaker 00

  And intentionality there is some, I have published a workflow, a document that helps you make that step, to make that elevation, like what are the issues?

• 58:28Speaker 00

  What are alternative ways to solve this potentially that I'm not seeing, et cetera? And what I try to do is I try to create that first time for my executive team as well. Cause it's not just me that suffers from this, it's most everybody. In fact, it's most PMs because PMs are so influential that it spoke of the wheel of product creation and product development. That we often, you know, you're, you're, it's a sine wave, right? You are discovering and shaping problems and then you are commanding and captain in execution. And it's endless and there are endless meetings. And so you need to create time for forest time for elevation. If you don't, you'll become less effective over time. It's just attrition.

• 59:14Lenny Rachitsky?

  And then just to make it even more concrete for people, what are examples of forest time? Is it taking time off? Is it advising on the side? Is it?

• 59:20Speaker 00

  It is taking a day off.

• 59:23Speaker 00

  At the end of a month, a full day or two days. And instead of just playing golf, although that's fine. It is doing a workflow, a worksheet to, to survey the forest specifically. And sometimes people, managers are like, wait, you're giving people a day off when they should be working harder and harder. And I think it's completely worth it. It's not about working harder, it's working smarter. It's about seeing more options than you see. And so I'm very happy to give that time to park managers, to product executives or design executives or engineering executives. Cause I think that if they do it properly, then we'll have better execution in the long run.

• 1:00:05Speaker 00

  Let's put it this way, we aim in, in, in product development, we aim for maybe like 10% of the time. And then we execute and build for the other side. It's not just, I mean, there's more stuff we do. If your aim is off, then you're, you're spending one, $2 million incorrectly of people's time. And so forest time should improve your aim. That's the entire point because your aim is a precursor to a huge amount of investment. And so I think it's, it was well worth it.

• 1:00:37Lenny Rachitsky?

  I love this. So specifically what you do with your team is once a month, you give them a day to do this kind of worksheet that you put together.

• 1:00:44Speaker 00

  Uh huh.

• 1:00:45Lenny Rachitsky?

  And then that worksheet is in this post that you wrote that we all point to. Is that right?

• 1:00:49Speaker 00

  Correct, correct.

• 1:00:49Lenny Rachitsky?

  Amazing. Okay, great. This is very tactical advice. I love it. Okay, one last question before a very exciting lightning round. You worked at Bridgewater Associates, which I didn't know until I started digging into your past. That sounds creepy. And Bridgewater Associates is famous for what Ray Dalio's hedge fund, author of Principles and all these other incredible books. And it's a very unique working environment. So I just wanted to ask about your experience there. Specifically, one of the craziest things there is just this thing called dots, I think it's called, where people just call out mistakes that people make at the company and it's public. Is that how it actually was? Any memories of that?

• 1:01:27Speaker 00

  Yeah, yeah. I was a senior management, what's called an SMA, which is the management layer right under Ray's team. And

• 1:01:39Speaker 00

  we were the priests of the church of Bridgewater. Bridgewater did things like record. This is public knowledge. I'm not saying anything.

• 1:01:50Lenny Rachitsky?

  Yeah.

• 1:01:50Speaker 00

  Recorded every meeting. Eventually, we created a dot collector, which is allows you to rate people in real time. So I'm just having a conversation with you. And before the meeting closes, in front of each other, I pull up my laptop and I rate you. I rate the interaction. And you know, in theory, the idea is that if you constantly rate people across hundreds of interactions, then you build a picture of them that is fairly accurate, statistically accurate, that will transcend, you know, maybe like emotional relationships as a wisdom of the crowd idea. So that's a theory. In practice, it is emotionally like exhausting.

• 1:02:34Speaker 00

  And like you said, a little creepy, even the recording. So I think there were things about Bridgewater that I didn't had understood intellectually in terms of the purpose that Ray had designed, but didn't quite work. It's like,

• 1:02:49Speaker 00

  the way I think about this is.

• 1:02:53Speaker 00

  The theory of the principles are really good. The practice can be quite and the execution can be quite off and not uh very human or not very empathetic. But I will say this, Bridgewater taught me things that I don't think any other organization in the world have taught me. Like, one example is Bridgewater thinks of people in three dimensions, their skills, their attributes and their values. Most organizations think about people in terms of just their skills. But it makes sense that people have attributes and values, right? That people are, you know, uh timid, people are bold, people like to jump in, people like to stand back.

• 1:03:37Speaker 00

  And, you know, all those other things we think about personality and proclivity. Uh Bridgewater tries to establish and measure them. And also tries to write job descriptions that say this is the kind of attributes we're looking for, not just the skills we're looking for. And then, of course, values, like, you know, are you a thief? Or are you principled and so on and so forth? Now, that idea of looking at talent or people in general, both in your professional life and your personal life, is a huge addition to me as a professional from Bridgewater. So I am not by any means saying, I'm saying that there were things I didn't enjoy about Bridgewater, but things that I learned that I've learned nowhere else as well.

• 1:04:18Lenny Rachitsky?

  Did you take that to what you do today, thinking of people in those three different ways? And

• 1:04:23Speaker 00

  Hundred percent. In my, in my professional life, in my personal life, uh when I interview people, I am cognizant of those three things. And I try to extract those three things because I think it improves your success. You know, famously, like, all the weird skill-based interviewing at Google was only fifty, you know, fifty fifty predictive. And the reason is Google did not consider the other two things, I believe. Right? You know, Bridgewater was willing to endure eighty percent attrition to arrive at the best people. Now, I don't think it works for them because some of their system was not empathetic of humans, like expecting humans to be computers. But I thought that was a very important insight.

• 1:05:07Lenny Rachitsky?

  Awesome. Ajay, is there anything else that you want to share before we get to our very exciting lightning round?

• 1:05:14Speaker 00

  In the history of product development, we have Basically start to create abstraction to guide our work, right? Versus wild, the wild, wild west. So the engineers came up with agile and pair programming and all these things. The designers have come up with, you know, design thinking, design sprints, and combined with research to talk about how to do discovery of various complexity. And the question is, the product abstraction, so there's code, there's product and there's business. So the product and business layer, what is our abstraction? What is our crucible for organizing our work? We don't even have one. We don't have a name for it.

• 1:05:56Speaker 00

  And so the idea of a product system is that there's an abstraction above agile and design thinking that we have to pay attention to how to build solid organizations and to execute well at the product and the business layer. This is a co-created framework with me and Azina. And the idea here is how do you construct a good product system? And literally, you could boil it down into a checklist of the systems you need to build to build a really good cohesive R and D organization. So I think that's the tee up. I'm going to have to leave you thirsty because someone else is probably going to go deep into it.

• 1:06:35Lenny Rachitsky?

  Amazing. And that's your wife that you mentioned, who you are co-creating this framework with and who we're going to have on the podcast in the future.

• 1:06:40Speaker 00

  That's right.

• 1:06:41Lenny Rachitsky?

  What is it like being married to another product leader? Would you recommend?

• 1:06:45Speaker 00

  A hundred percent. You're going to have really, really productive conversations and you can, you can redesign other companies' applications in one conversation in the evening.

• 1:06:57Lenny Rachitsky?

  Amazing. Well, that was almost the lightning round question, but I moved it up earlier. And so with that, we've reached our very exciting lightning round. Are you ready?

• 1:07:06Speaker 00

  Yeah, I'm ready. Let's do it.

• 1:07:07Lenny Rachitsky?

  Okay, great. Let's do it. What, what are two or three books that you've recommended most to other people?

• 1:07:13Speaker 00

  There's one business book that I recommend. I think it's called The Halo Effect. It's basically a book that lets you call bullshit on all these business books that are, tell you all kinds of stupid shit. It is how to deconstruct what is important in a business and self-help book and what is not important and what is just circumstantial storytelling with random facts and form-fitting evidence. It's called The Halo Effect. Read it. Why do you need to read it? Because.

• 1:07:43Speaker 00

  Garbage in, garbage out. You know, people were amazed that the outlier effect, Malcolm Gladwell. And then people have been tearing it down for 15 years now. But everyone ingested it and and thought it was the most important thing. But how do you, how do you know what's important to take away from them and what's not? The halo effect will help you. And then the other thing is I read for pleasure because I read a lot for work. And so, science fiction is the thing. There's lots to recommend, but I would say that people should either read Dune, Frank Herbert, or Foundation by Asimov. If you haven't read those two things and you're a science fiction person, you really should. The wall building is incredible.

• 1:08:25Speaker 00

  It's not, you know, I understand Tolkien and fantasy, but the science fiction side of it is those two books.

• 1:08:31Lenny Rachitsky?

  There's also a TV series, A Foundation, now, which I can't say recommend absolutely, but it's, it's a beautiful show.

• 1:08:39Speaker 00

  Yeah, no, I, I haven't watched Foundation yet. I, I just felt like, I just felt super weird watching it after reading it. And I could only make it through three quarters of Dune version, you know, part one. But I will make it through them. I don't expect them, the books are glorious. If you love prose, the books are, man, crazy. But I will get through them eventually.

• 1:09:04Lenny Rachitsky?

  I've not actually read Dune, but the movie was incredible. I played the video game Dune where you're just mining spice all day and it's stuck in my brain forever.

• 1:09:13Lenny Rachitsky?

  Okay, next question. What is a favorite interview question that you like to ask candidates that you're interviewing?

• 1:09:18Speaker 00

  I try to ask two, I feel this is, I feel like it's gonna give people a cheat sheet when I interview them. But I, I try to ask two questions. So I'm, I'm not a person who does favorites, so it's hard for me to pick favorites. But I ask people to introduce themselves and I think it tells me a lot about them. How they tell about themselves, what they say about themselves and the content of it. I ask people about the things they think they're truly great at. And then I ask people other things they think they need to learn. Uh, about in the pro- for the latter two is about their professional skill, their craft. Um, I think it tells me a lot about how they communicate. It tells me a lot about how thoughtful they are.

• 1:10:04Speaker 00

  It tells me a lot about what they're proud of and what they lead into, and those kinds of things are very important to me.

• 1:10:10Lenny Rachitsky?

  What is a favorite product you recently discovered that you love?

• 1:10:13Speaker 00

  I have been optimizing my workspace a lot. So I'm on a kick right now where I I use Windows, you know, I I I was in Windows PM and I still have my Windows box. But a lot of people, we use Macs at work and I've used Macs for the last few years. So even though I switch between them, I've spent a lot more time on Mac and my Windows experience is completely optimized, like it is perfect. Well, Mac, I'm like, the windowing sucks, there's all these gaps I see. So I've been trying to figure out how to dial in my Mac experience. I've been, you know, I hate the activity monitor sucks, like what's a replacement? You know, the sound, it doesn't support uh, sound through HDMI

• 1:10:59Speaker 00

  or sound through, I don't know, just some weird setup. So I've been optimizing that. One particular product I like in the context of that is unlocks. It's a like one man product that allows me to just look at my phone and log into my Mac when I walk up and then locks it when I walk away. And it actually detect my proximity, so it'll start the login process while I get close. I think that's incredible and I feel like it improves my productivity.

• 1:11:25Lenny Rachitsky?

  Very cool. Sounds like a lot of haterade for Macs over here.

• 1:11:29Speaker 00

  Well, for someone who uses it a lot, uh, no, I think it, you know, pros and cons. I'm not, I'm no longer paid by Microsoft, so um, I have things I don't like, but there are also things that, you know, the Mac isn't perfect either.

• 1:11:42Lenny Rachitsky?

  Yeah, indeed. What is a favorite life motto that you repeat to yourself or share with other people, either in work or in life, that you find valuable?

• 1:11:52Speaker 00

  I've taken to saying that there's more knowledge outside my head than inside it. And this is a plea for curiosity. I have three main things that I that are my north star personally. But also, when I say personally, I mean everything, including professionally, which is originality, curiosity and wisdom. And so this thing about there's more knowledge outside my head than inside my head is a plea for curiosity. It's a plea for skepticism. It's a plea to be humble about what you know, no matter how old you are, about the world around you and always be listening for more.

• 1:12:36Speaker 00

  Even when you know something, let other people speak because they might add 10% more to the 90% you know. And so being an active listener is very important.

• 1:12:48Lenny Rachitsky?

  Beautiful. Last question, you are from Nigeria. What is a Nigerian food that you think people need to find and get ASAP?

• 1:12:57Speaker 00

  I will recommend two, depending on how familiar you are. So if you've never had fried plantain with beef stew.

• 1:13:06Lenny Rachitsky?

  Oh, man, that sounds great.

• 1:13:09Speaker 00

  You should stop what you're doing, stop work. Whatever you're doing, find your next Nigerian friend and go get some. Okay. This is the food that most Nigerians will basically trade years of life to have access to. Okay, so that's what I would say. And then the the second thing is,

• 1:13:35Speaker 00

  if you really want to go, you know, if you want to be in the in club in Niger, as we call it, you gotta try pepper soup. Now, if you're not into spicy stuff, I'm sorry, the door is closed to you. But pepper soup is really in. And it is amazing. It'll make you sweat, but it's delicious and you should give it a shot.

• 1:14:04Lenny Rachitsky?

  Ajay, I think we've solved many people's sharp problems. I really appreciate you making time being here. Two final questions. Where can folks find you online if they want to reach out? And how can listeners be useful to you?

• 1:14:16Speaker 00

  I publish on Substack when I have time. You should check it out. It's usually all about things that are beneath the surface. What's behind the thing? I believe that's how you'll find it. I'm on Twitter as well. So you can follow me because I will talk about products. How you can be useful to me is go follow me on Twitter, sign up for updates on the book. If you do, I will draw from that audience to help name the book, to help design the cover for the book. The book is intended to have a freemium because I want this book to be available to people in Africa and India across the world. So there'll be a free version

• 1:14:59Speaker 00

  of it. And there'll be premium versions with more tools, more help, and maybe even like interviews with luminaries that you care and love as well. And so that hopefully that will fund the free side of it as well. So come in, become part of the party, maybe join a pre-read, an early, early draft read. That is the best way you can help. So it's a call to all PMs and people of goodwill.

• 1:15:29Lenny Rachitsky?

  Amazing. What a great answer to that question. I'm gonna go get some pepper soup and some plantain beef meals. Thank you so much for being here and I'm gonna go get some food.

• 1:15:41Speaker 00

  All right. Thank you, Lenny. It was super enjoyable one. Love hanging out and Godspeed.

• 1:15:48Lenny Rachitsky?

  Bye, everyone.

• 1:15:50Lenny Rachitsky?

  Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.